STEREOSELECTIVE ADDITIONS OF CHIRAL ALPHA-SULFINYL KETIMINE ANIONS TO ENE ESTERS - ASYMMETRIC SYNTHESES OF INDOLO[2,3-A]QUINOLIZIDINE AND YOHIMBAN ALKALOIDS

被引：66

作者：

HUA, DH

BHARATHI, SN

PANANGADAN, JAK

TSUJIMOTO, A

机构：

[1] Department of Chemistry, Kansas State University, Manhattan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 25期

关键词：

D O I：

10.1021/jo00025a011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The in-situ 1,4-addition/ring-closure reactions of chiral alpha-sulfinyl ketimine anions with acyclic and cyclic ene esters offer a simple, convenient route for the construction of chiral cyclic alkaloids having a nitrogen-atom ring juncture. Asymmetric induction in the conjugate-addition reaction of the carbanions derived from alpha-sulfinyl ketimines possessing chiral sulfur with various cyclic and acyclic ene esters, subsequent ring-closure reaction, and reduction of the resulting beta-sulfinyl enamides were utilized in the syntheses of (-)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a] quinolizine [(-)-1], (-)-alloyohimban [(-)-2], (+)-3-epi-alloyohimban [(+)-3], and (-)-yohimban [(-)-4].

引用

页码：6998 / 7007

页数：10

共 57 条

[1]

AKIMOTO H, 1974, CHEM PHARM BULL, V22, P2614

[2] FURTHER INVESTIGATION OF THE NATURE OF THE C-LI BOND - STRUCTURES OF A PHENYLTHIOMETHYLLITHIUM COMPLEX AND OF A METHYLTHIOMETHYLLITHIUM COMPLEX [J].